Hopkinton
Trail Running Calendar near Hopkinton 2026-2027
Explore the top trail runs near Hopkinton for 2026-2027! We've gathered 26 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Trail races in Upton State Forest: a single-loop 10.5K and a two-loop half marathon with about 720 ft elevation per lap. Technical single track and forest roads, aid stations roughly every 3 miles, plus post-race fire pits and hot soup.
A family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.
A hilly 5K at Pine Banks Park supporting Melrose High School cross-country, with awards by overall and age group and post-race refreshments.
Group trail run for women and nonbinary participants on a roughly 3 mile loop in the Fells near Winchester MA at a comfortable conversational pace.
A six hour timed trail race on a rocky 5K loop at Wright Locke Farm with a cupless aid station, goat companions, a $35 entry, and limited registration.
A community trail event at Good Pickin’ Farm with a scenic 5 mile run, a 2.5 mile walk or run, and a 1K kids run plus post race farm activities.
Trail races of 5.3 miles and 10 miles through Callahan State Park finishing at Brophy Elementary School in Framingham, with mile markers and commemorative gifts.
A multi terrain 5K, a scenic 2 mile walk and a kids loop at Old Sturbridge Village on November 15, 2026 with awards and participant shirts.
A scenic 5K trail run in Wrentham, MA on November 26, 2026 with awards, post-race donuts and cider, a raffle, and a $25 registration fee.
Trail trail races in Cumberland RI on Nov 28, 2026 with a kids 1 mile, 5k, 5 mile and a 4 hour multi lap option using chip timing.
December 2026
A 20th edition December event in Melrose featuring a changing 3.5 mile cross-country race and a 2 mile non-competitive walk with team and individual awards.
Trail event in Cumberland, RI offering kids 1 mile, 5K, 5 mile and a 4 hour multi lap with chip timing and marked courses.
January 2027
Winter trail event at Hale Education in Westwood MA offering a 30 hour race and a 15 mile looped course with marked trails, cupless aid stations, and required cold weather gear.
March 2027
Trail races at Monastery Trails in Cumberland, RI on March 14, 2027 offer distances from a 1 mile kids run to a 100K 12 hour ultra. Team ultra entries and a multilap 5 hour option are available and all finishers receive a medal.
Trail Animals Running Club hosts 6 hour and 3.5 mile loop trail events at Hale Reservation in Westwood, MA with marked trails, cupless aid, and limited parking.
April 2027
An obstacle course race in Cumberland, Rhode Island featuring a 3.2 miles course with about 1,000 feet elevation, multiple wave formats including elite and age group competition, multilap sessions, and a 12 hours ultra option.
TARC Spring Classic in Weston, MA offers 10K, half marathon, marathon and 50K on a marked looped trail with one cupless aid station.